Kissing Frogs and Catching Princes
by PeachyKeen83
Summary: When wealthy socialite Blair Waldorf lays eyes on the new boy in school, she decides Chuck Bass must be hers. However, the new social god plays the game just as hard as she does. Enter Dan Humphrey - a lonely boy looking for money for college and an excuse to wreak a little havoc. Could this social outcast be just what the Queen of Constance needs to finally land her prince?
1. New Faces in Familiar Places

**Kissing Frogs and Catching Princes**

 _Dedicated to all the girls who have kissed a lot of frogs on their quest for something better._

 _May you one day find your Prince._

 _Happy Valentine's Day_

 _xoxo_

 **~x-X-x~**

 **Chapter 1: New Faces in Familiar Places**

Dusky Louboutin pumps pounded the graying pavement in quick succession. _Click,_ _ **click**_ _. Click,_ _ **click**_ _._ Powerful navy fabric swayed in the breeze, tickling creamy thighs. Ivory knee-highs attached themselves poetically and ran down svelte legs, imprisoning them. The wind swept soft chocolate tendrils across covered shoulders, a slight shiver escaping nude-glossed lips as two delicate hands reached over and wrapped the charcoal blazer more tightly around a shivering frame. Turning the corner, mysterious eyes sparkled a little with recognition, a small smile gracing plump lips as a hand reached up and waved through the air.

"Serena! _Serena!"_

Turning towards the voice that called her, Serena van der Woodsen smiled and waved back at the beautiful and familiar girl before her. Striding up to meet her, the blonde wrapped her long arms around the brunette's tiny frame and happily pulled her close, giggling like a little school girl.

"Blair! I've missed you so much!"

Looking up at her sparkling blue orbs, Blair Waldorf had to admit that an entire summer without her best friend had been dull to say the least. Where Serena had been traveling the Caribbean on her latest exotic adventure, Blair had been busy improving her social calendar in New York City, working as an intern for a successful mogul who ran a string of hotels globally. It was a risk to work rather than enjoy her last summer before final year of school, but Blair had wanted to hit the ground running. Her mother had always said that time waits for no man. _Nor woman_. So she had successfully carried out a hectic schedule throughout the long summer months, earning not only a commendable list of extra-curricular activities to woo future colleges, but also recognition in the Upper East side as more than just the wealthy daughter of a famous designer. Blair Waldorf was a multitasking Queen who didn't understand the prospect of slowing down. _No pain, no gain_.

There was a reason she was considered a wonder-woman. Or over-achiever.

 _She preferred the first term._

"So, tell me all about your tropical oasis getaway. Was it all cosmopolitans and cabana boys?"

Serena smiled, a sparkle glistening in her eyes which told Blair straight away that her idea of living vicariously through Serena was a good one. Sure, she had missed the partying season with the town's most notorious party-girl, but she knew her blonde bombshell best friend would have had more than enough fun for the both of them. Where Blair was meticulous and organized, Serena was carefree and flighty, preferring to live life jumping out of the plane rather than flying it like Blair. She thrived in scenarios of unpredictability and the whimsy that came with going with the flow. _Organized chaos_ , as the energetic blonde liked to put it. Ethereally beautiful, Serena was the most wanted and most gossiped about "it" girl in Manhattan. However she was also probably the most dependable person is Blair's life. Although she was popular she never let it get to her head, and being friends since the age of five had allowed both girls to grow in different directions but still maintain a healthy respect for one-another.

 _Serena was Blair's rock, as Blair was Serena's._

"More like martinis and muscle men," Serena laughed, wrapping her arm in Blair's. The blonde was notorious for becoming easily bored by her male counterparts and not pursuing committed relationships, in spite of the long line of eligible men wishing to date her. Blair however, was completely different, forever wishing for her prince charming to come and whisk her away for a romance worth writing about. For now though, she would settle for Serena's tales of lust and intrigue across the seas. As they made their way down the road towards school, Serena eagerly chatted away about her new-found appreciation for older men. "Boys are _so_ last season, B. I'm onto a new breed of male now. _Men_."

"Hmmm," Blair replied thoughtfully, tilting her head to the side as brilliant flashes of white streaked their way across the shadowed streets, the morning sun lighting the city canvas. "I think you may have a problem finding any of those at school."

School was in fact the Constance Billard School, a private and elite all-girls institution in New York City. Located at 93rd and Madison Avenue on the prestigious Upper East Side of Manhattan, it housed the city's elite. The children born and bred by society's most affluent. Alongside the girl's school lay their brotherly counterpart, St. Jude's school for Boys, allowing the social matriculation of both boys and girls. Boys being the operative word, one which Serena frowned at when Blair mentioned the fact.

"Well, it's a big city. I'm sure I will make some use of it!"

Clasping her fingers around her friend's, Serena pulled Blair along the bustling streets and straight towards the school's entrance. Smiling at the usual crowd of adoring admirers, the school's Queen Bees skipped up the cemented stairs and into the bustling halls. Crowds of students greeted one-another with hugs and squeals, Serena rolling her eyes when notorious arch-rival Vanessa Abrams, veered past them with a look of disdain. Leaning against the coolness of the metallic lockers, Serena reapplied her lip gloss as Blair placed her books within, a meek voice chirping at them from behind.

"Good morning Blair, Serena. I trust you had a great summer?'

Standing in the hall, the tiny girl shuffled about on the spot nervously. Biting her lower lip, her straight blond hair grazed her shoulders with each movement of her tiny head. Holding a large folder to her chest, she waited anxiously for the girls to speak.

"Jenny," Blair replied, forcing a smile across her lips as she looked down at the wide-eyed junior. "I trust you were able to book that table for dinner tonight?"

Nodding ferociously, Jenny reached down into her folder and pulled out a large piece of paper. Reading over it meticulously, she recalled all the information she had jotted down previously.

"Yes, dinner for two at _Louis_ for eight o'clock. Window seat verified. The limo will swing by and pick him up at seven-thirty sharp."

"Him?" Serena chuckled, nudging Blair in the ribs as the brunette sighed in contempt. Glaring, she ordered the flighty blonde to hush for the time being as she returned her attention back to the young girl.

"Good work Jenny. Now I need you to go Waldorf's and pick up the dress that will be waiting there for me. Tell them I sent you and that I need matching shoes. They'll know what to do. Also, run by the Penthouse and ask Darota to double-check that the theater tickets will be ready for us when we arrive. Box, not booth. They messed it up last time and my guest was most seriously displeased."

Writing down the orders in haste, Jenny mumbled to herself as Blair and Serena both looked down upon her. Finally finishing her scrawl, she looked up and smiled, blowing her blonde fringe out of her eyes with a soft breath. As people rushed frantically by them, the three girls stared at each other for a while in silence. Finally, unable to take the weirdness any longer, Blair rolled her eyes and ushered Jenny with her hands.

"Go, go, go. That's all I need right now."

Nodding, Jenny's face fell a little as she reached down for her bag, Serena throwing her a sympathetic smile before turning her attention back to Blair. Twirling a long strand of golden hair between her fingers, the blonde looked down at her brunette sidekick with a questioning look.

"What?" Blair stated, giving Serena a look of complete indignation.

"Do you think maybe you could go a little easier on the kid?" Serena quipped, the bell sounding out above them as students began shuffling towards the hall. "You've been running her ragged all summer."

"If she wants the title of Queen Bee next year," Blair stated, her hand clasping a folder and sliding it so that it rested parallel to her hips, "then she needs to earn her stripes. Just as I did."

"You were born into the position," Serena countered, rolling her eyes at Blair as they neared the school's hall entrance. "You hardly worked for it."

"And you've hardly worked," Blair chided her friend sarcastically, scrunching her nose up as the blonde squinted her eyes in return. "See, there's a reason we're friends after all, S."

Sliding into the hall, the pair were watched as they took their seats among the evenly distributed pews. The crowed hustled with the usual excitement of the first day back at school, whispered voices drifting gossip between the students like snow sprinkling down at Christmas. Soon enough, the St Jude's boys made their way into the hall and began taking their places, the sound of sweetened girly giggles filtering through the hall. Feet shuffled in quick succession, Blair looking up to see Nate Archibald making his way to the pew across from theirs. He smiled when he saw them, magnificent baby blues gazing in kindness.

Nate and Blair had always been close friends, their parents having often summered together in various holiday retreats around the world. Nate's father was their accountant, and a very successful one at that. Everyone within a two-mile radius was after him, and his reputation exceeded anyone else in the same line of work. His mother often worked on social events with both Blair's and Serena's mothers, so the three of them were always forced together at the numerous society shin-digs that took place.

Blair often thought of them as the three amigos. A _close-knit,_ _ **trustworthy**_ group.

As the girls waved over at their handsome friend, the headmistress stood at the microphone and cleared her throat, all eyes drawing upon her as the congregation settled down.

"Good morning boys and girls and welcome back to what we hope to be another extremely successful year at Constance Billard and St Jude's. We trust you all had a relaxing summer vacation and have come back prepared to work to the utmost standards this schooling year."

Shuffling in her seat, Serena was already getting bored. Glancing across the room, her eyes landed on Nate and she pulled a face, the young boy trying desperately not to react. He cleared his throat and sent her a playful warning look, the blonde scrunching up her nose before turning away. Leaning into Blair, she waited for the headmistress's eyes to move away from her general direction before she whispered.

"So, tell me about this " _date_ " Miss Waldorf."

Without moving her eyes from the headmistress, Blair muttered under her breath, seemingly un-phased by the blonde's question. With the voice of the principal muttering around them, the brunette spoke in a low hush.

"It's the boss's son. He's just come back from studying abroad. His father needed someone to take him out for the night, I offered. No big deal."

" _The common room in the West Wing is for Seniors only. Please, if you are not there to study or have a relaxing break between classes, then do not use this facility."_

Serena nodded, a slight smirk sliding across her lips as she continued.

"The boss's son. Wow B, I didn't know you were so naughty."

"Oh please," Blair responded, doing her best to sound bored with the entire conversation. "It's not a big deal. I managed to secure a great deal for my mother's charity benefit simply by agreeing to go. It's just dinner and the theater and in return I managed to get two whole tables sold for my mother's benefit."

" _Swimming tryouts are at the end of next week. Please write your name on the board outside Mr Jefferies room if you wish to try-out for the team."_

"Sounds ideal," Serena replied, shuffling a little closer to Blair as the headmistress continued to prattle on before them. "Always the business woman. No time for love?"

"Love?" Blair scoffed under her breath, shooting a sideways glance at Serena before returning her gaze to the front. "Look, I'm not like everyone else here. I want romance, good looks and charm. Someone sophisticated and business-minded. Someone strong and independent and unafraid to say what's on his mind."

"Someone like you?"

"Someone who can match me," Blair countered, closing her lips as the older woman on stage continued her speech. "And I highly doubt a boy with a father like the man I have been working for all summer would fit the bill."

"Why is that?" Serena questioned, clearly enjoying the stirring of her best friend. "Not enough money?"

" _All social and charitable events must go through the social club committee. Please see Miss Blair Waldorf, head of the committee, if you wish to join and make a difference."_

"More money than he knows what to do with," Blair continued, smiling as the headmistress looked over at them. As soon as her eyes darted away, the brunette proceeded to finish her sentence. "But there's no warmth there. Plus, have you _seen_ the guy? His face is so hard, it could be hereditary. His son could look just as hard, if not, more so. That would not match with my soft complexion and features."

"Maybe not," Serena exclaimed, her soft velvet voice hitting her friend's ear with encouragement. "But, he could be drop-dead gorgeous and totally worth your time."

" _Now I wish to welcome all the new enrollments at Constance and St. Jude's. Please make sure you make each and every one of our new members feel most welcome."_

"Would you like to go on this date?" Blair offered, raising her eyebrows as Serena giggled by her side. "You seem more into it than I am."

"No can do," the blonde replied coolly, clapping her hands as the headmistress began calling out the names of the new enrollments. "I already have a date tonight."

" _Sarah Albright. Welcome."_

"Then hush up about mine," Blair ordered, nudging her elbow into the chuckling blonde's side. Serena giggled quietly but relented, placing her hand over her friend's as they both stared ahead. A short girl with wild red hair and freckles galore stood up from her chair in the front row and turned around, allowing the entire student population to see her. Shrugging, Serena turned back to Blair, a questioning look crossing her features as she lowered her brow.

"Hey, what did you say his name was again?"

Blair turned to Serena and smiled, thankful that she had dropped the sarcasm and was actually willing to talk.

"Charles Bass."

" _Charles Bass. Welcome."_

Two pairs of astonished eyes darted up at the mention of the name. Stretching their necks, the two girls glanced over at the boy who stood in response to the name. A quick glance told them everything they needed to know. Her mind working in overdrive, Blair took in every ounce of information that she could from this quick introduction. He was tall, raven hair slicing across his creamy forehead in a jagged formation. His pixie-like haircut was matched by thick, furrowed brows, hanging dangerously low as he waved at the crowd. Blair found it hard to determine if he was reserved, embarrassed or simply unimpressed with the greeting ritual. At any rate, his chocolate eyes gave little away, nor did his closed lips, soft and perfectly proportioned. Instead, together they served only to demonstrate a cool and calm exterior. He oozed a sense of power, something Blair found quite impressive.

"Oh," Serena said, seemingly impressed by what she saw. "Looks nothing like daddy-dearest at all."

She was right, everyone knew it. As soon as he stood the crowd buzzed a little with excitement. Standing there in just a school uniform, there was an understated sex appeal that came with him. The lemon shirt looked almost designer, the school's neck tie draped around his neck like a Hugo Boss billboard in Times Square. Even the tan pants that were chastised by all had managed to look like they'd been specially made for him. He'd even gone as far as to make his own fashion statement regarding the mandatory attire, a carefully knitted patchwork scarf that showed of the vibrant colors of charcoal, maroon, ivory and red. Checkered across his blazer, he was the epitome of sophistication.

 _Not at all what Blair had expected._

Watching her, Serena smirked a little as the boy smirked and then sat with Blair's undivided attention, the brunette's mind clearly working in overdrive at the prospect that was Charles Bass. Playfully nudging her shoulder into the side of her best friend, the blonde waited for nervous orbs to gaze upon her in reply. Sure enough, after a moment to gather her thoughts, Blair turned and leaned into Serena as the headmistress continued with her new-arrivals roll call.

"New plan," Blair announced, grabbing out her blackberry and typing away furiously. "Theater and a movie will not suffice. I must throw the best " _Welcome Back To School_ " party the Upper East Side has ever seen."

"And why is that?" Serena teased, scrunching her tiny nose together as her friend gazed at her in exasperation. "I thought it was no big deal, this date with Charles?"

"That was before I laid eyes on him, when he was nothing more than a Trust-fund _Brat_ who looked like a recreation of Steve Urkel amalgamated with Bill Gates. That-" she murmured, pointing in the direction of Charles, "That my friend, is a whole new ball game!"

"So what happens now?"

"Now," the brunette announced, slipping easily into her planning mode. "Now I must get organized. I'll need to get Jenny straight into planning, call Darota and have her organize the food, and get the minions to make sure anyone who's anyone is on that list and making an appearance at my party tonight!"

"And what about me?" Serena asked, turning as the headmistress thanked them all for attending and wished them a wonderful year. "What can I do to help you?"

"You, my dear, sweet vixen of a friend," Blair replied, smiling sweetly at Serena. "You can find out everything there is to know about Charles Bass!"

Nodding her head in understanding, the leggy blonde got to her feet and held out her hand, the brunette completely unaware that the assembly had come to a close and the students had begun filing out of the hall. Sending them a quick wave, Nate made his way to the front of the hall and shook hands with Charles, much to Blair's delight.

"And it looks like you can start by interrogating Nate"

Glancing across the hall, Serena's eyes landed on the two boys conversing, smiles all around. They shook hands, and Serena knew at once that whatever information there was to get, she would surely be able to extract it from Nate.

"Done and done," the blonde stated happily, shaking Blair's hands as the two exchanged smiles. "Looks like Princess Blair may have finally found her Prince!"

"Serena, my dear," Blair cooed happily, chocolate orbs looking to the heavens with a thankful gaze as she wrapped her arm around the blonde's and headed towards the door. "I think you just might be right!"

 **~x-X-x~**

 **AN:** So I'm giving this story another go because I kinda loved writing it and thought "What the hell?" I am totally, completely and utterly a DAIR shipper. I used to be Chair up until he sold her for a hotel. I just couldn't get around that. Chuck treated Blair like a prostitute and I couldn't forgive that. Anyway, this is completely AU and I'm not even sure who I will write into it but please let me know your thoughts, opinions and of course – what you want to see?

Much love, and please review!

 **Chrissy**

 **xox**


	2. Open Season for the Close-Minded

_**AN:**_ _A big thank you to the people who reviewed this fic. I know that it's AU and gone back to the beginning, but it's great that you decided to take this journey with me :) As I said in my first chapter, I am a Dair shipper. I'm not entirely sure where this will end up, I've only got a vague outline in my mind, so all thoughts, opinions and ideas are more than welcome. I'm happy to return PM messages too because I love a good chat, especially about the shows and ships I love!_

 _Anyway, I hope you all enjoy the latest update!_

 _Chrissy_

 _xox_

 **Kissing Frogs and Catching Princes**

 _Dedicated to the thoughtful reviewers who made my day when they took the time to let me know their thoughts._

 _You are all wonderful xo_

 **~x-X-x~**

 **Chapter 2: Open Season for the Close-Minded**

The warm, midday sun sprawled across the crisp blue sky, unafraid of the sporadic light-grey clouds that passed by it in the gentle breeze. From its position, the amber ball cast its warmth over the bustling quadrangle of Constance Billard, hitting each body as they made its way forward across the hardened asphalt. Fumbling with her bag and books, an obscure and tiny blonde scrambled across the perfectly aligned cement in a hurry. With a quick blow of air from the side of her mouth, she sent her wayward bangs out of her eyes and pressed forward. Sitting before her in their usual lunchtime spot were the Queens of Constance, Blair Waldorf and Serena Van Der Woodsen. _God, even their names sounded royal_. Flanked by their usual posse of admirers and go-getters, the two girls were the most prominent of the small circle. Even if you weren't looking in their general direction, you could still feel their presence. Letting out a large puff of air, Jenny Humphrey longed to be a part of that special social circle that others envied. She'd dreamed of moving on from her Brooklyn background and being considered one of the more popular girls whom everyone wanted to be. She just had to make Blair so incredibly happy that the sharp-tongued brunette would notice her, see how much she wanted this, and shine a little acceptance her way.

 _And the paper in her hand might have been just enough to at least get her foot in the door!_

Heels clicked across the grey cement in a frantic beat, knock-off Jimmy Choos pounding the pavement hard. Jenny knew she'd never have the money to afford the real things, but thanks to she was able to at least try and look the part. Breathing heavily, she descended on the chatty group of beautiful people and screamed to a halt, Blair turning to look at the scrambling blonde with a look of slight distaste. Raising a brow, they all waited patiently for the breathless blonde to gather herself and catch her breath. Out of the corner of her eye, Jenny saw a slight smile gracing Serena's lips, the flighty blonde the most relaxed and kind of the group of girls before her.

"I... I have... I have _news_..."

"Well spit it out, minion!" came the barking reply from Blair, the brunette closing her eyes and taking a deep breath after a severe look from Serena made her change tact. "I mean what kind of news Jenny dear?"

"I have news... news about..." Blair struggled to keep the pained look from her face, but her lips remained sealed shut and even produced a forced smile for the breathless blonde's benefit. "About Charles Bass!"

 _That got her attention!_ Twirling around from her spot on the highest step, Blair ushered the young girl closer to her as the girls around her hummed in enthusiasm. With a click of her fingers, Blair sent for the dark-haired girl sitting below her to give her the water bottle in her hand. Without hesitation, the Evian bottle was within Blair's grasp and surging toward Jenny in an attempt to help the young girl catch her breath as much as possible. Clearly, whatever she knew about the new boy at school was worth its weight in gold. As the icy water hit her lips, Jenny felt instant relief and allowed the liquid to cascade down her throat slowly. Truth be told, she enjoyed being of some importance to these people at this point in time.

"Well, I was sitting in the library behind the stacks in the East Wing," the girl stated excitedly, handing the water back to Blair who tossed it to the girl behind her. "And I found out he doesn't like to be called Charles, he prefers Chuck."

"Chuck," came the thoughtful response from Blair, chocolate orbs lively darting back and forth as if processing the very simple piece of information handed to her. "I much prefer that to Charles, don't you S?"

"Seems less _old_ ," came the nonchalant response from the blonde who had now leaned back on her palms and opened her glorious body up to the even more glorious warmth of the sun. "Definitely more fitting."

"Definitely," Blair agreed, turning her attention back to Jenny. "And what else?"

"He now resides in the Penthouse suite of the Empire hotel and he used to live in the Upper East Side until his father sent him overseas for school. There seems to be a story there as well, but he didn't express anything to the librarian. More like, evaded the story by commenting on her blouse."

"He commented on Mrs. Haggley's blouse?" came the disgusted response of the girl sitting behind Blair. "He has no taste then, surely!" Blair rolled her eyes at the response, Jenny understanding this look better than anyone. Someone had missed the clue in the story somewhere.

"Or," came the retort everyone knew was coming, "It means he's smart enough to know how to distract someone's attention away from himself by flattering them and turning the conversation towards them." She glanced in Serena's direction, the blonde sending her a wink of agreement. "And, it also goes to show that he has an idea about fashion. Look at the way he was dressed this morning for heaven's sake."

"Um, he was wearing the school uniform Blair," came the reply from Penelope, ambitious for a girl who had a habit of putting her leader down. "I hardly think that qualifies as fashion sense." A scathing look from Blair quietened the disagreeing statement from the girl beside her.

"Hugo Boss tie with his own initials sewn in? And that scarf, school colors but setting off its own statement? Definitely a show-piece and only one who enjoys the elements of design and fashion would be able to wear such a piece and know how to work it." The words were out of Jenny's lips before she could stop them. With the turning of Blair's head, the young blonde was sure she was going to receive the same angered look from the Constance Queen. Instead, she was met with eyes of approval, a real smile gracing Blair's lips as she nodded her head happily at the younger girl's remark.

"Precisely Jenny. I see I've underestimated your knowledge of fashion, even if you do wear Internet bargains around your ankles." Pulling her feet to the side, Jenny hid her footwear beneath her slim body. "And all this information means this is no ordinary boy we're dealing with here. This means we're dealing with someone who is smart, fashion forward and-"

"-a dear old friend of Nate's."

Turning around at the sudden voice which entered the conversation, all eyes rested on the stunning blonde who was stretched out before them. Serena's eyes remained closed, yet she knew they were watching her, a small yawn escaping her perfectly glossed lips. Upon hearing Blair's slight scoff, she proceeded to turn and force her brilliant blues upon them, such power behind them it was no wonder she managed to have all the boys drooling. Raising a delicate eyebrow, she stared at the girls as if she had no idea why they were watching her. "What?"

 _Serena van der Woodsen was perhaps the biggest tease on the planet!_

"Oh don't _what_ us, S," came the hurried response, Blair immediately reaching out and tapping her friend gently on her shoulder. "Divulge what you know."

"Well, you asked me to speak to Nate, and I did."

Another yawn escaped her lips, only to be met with another slap from her friend, this one a little harder. Chuckling, the blonde raised herself from her outstretched position and sat up, sliding her famous legs under her even more famous body. "Okay, okay. Settle down there B." Gathering herself, the blonde smiled at her eager audience. "Nate informed me that he and Chuck go way back, like as far back as ankle biters since his father is Bart Bass' financial adviser." Reaching out with a delicate finger, she twirled her hair playfully as she enjoyed the girl's undivided attention. "So Nate knows absolutely everything there is to know about Chuck since it was _he_ whom Nate spent last summer with whilst in _Paris, oui_?"

Excited by the news, a smile formed across Blair's lips within seconds. Sliding closer to her friend, the brunette laid her hand on Serena's knee as she thought out loud. "So Nathaniel will be able to give us every little last detail regarding Chuck Bass, thus ensuring that this party not only meets his expectations, but _exceeds_ them!"

A wink from Serena sealed the deal. Suddenly infused with adrenalin, Blair's mind whirled with every little last job that needed to be done before the party of the year. If she was going to secure Chuck Bass, the latest bachelor on the market, then she was going to have to think fast and work even faster! Shooting a hand out toward Jenny, the fiery Queen spurted out a babble of frenzied words.

"Jenny, you must go to my mother's store and pick up the dress I had Darota place on hold for me. Then you need to get to my house and make sure every little last detail has been adhered to – decorations, party favors, DJ, security, guest list..."

Furiously, the young, eager blonde began to jot down every last word her senior barked at her, her hand a blur of frenzied motion. Upon hearing the last item on the list however, she looked upward and blinked, hopeful baby blues staring at Blair. Shaking her head from side-to-side, Blair knew what Jenny was fishing for, she just wasn't sure she wanted to give it out yet. Turning to her side however, the buxom leader was met with a flick of Serena's hands, urging her to give the poor girl what she wanted.

"Ugh fine," Blair growled, answering her friend even though no verbal words were spoken. "Jenny, you can come too."

Standing from her perch on the stairs, the blonde smiled triumphantly and showered the older girls with her heartfelt thanks.

"Oh Blair, wow, thank you so much. I swear I will have everything ready for you just the way you want it!"

"I hope so," Blair replied, an edge to her tone though it was hard to remain firm when the young girl was smiling at her with a huge, goofy grin. "Otherwise Jenny, heads will roll."

Nodding furiously, the blonde scrambled back over the cemented quadrangle in a hurry, people darting to the side and out of her way as she went. Sitting up quickly, Serena wrapped her arms around the brunette as she glared at the other girls with them, Penelope and Hazel getting to their feet quickly to carry out their usual chores of inviting guests. Leaning back into the embrace of her blonde best friend, Blair closed her eyes and allowed the sun to warm them both. Giggling, a light kiss was planted on her cheek as Serena cooed in her ear.

"You did the right thing, inviting Jenny. This party is going to be amazing, B."

"Of course it will be," came the faux-angered reply, a glance across the quad seeing her eyes land on the handsome form of Chuck Bass accompanied by Nate Archibald. Serena followed her friend's gaze, throwing a wave in Nate's direction when the boy turned and saw them. Turing to see who Nate was acknowledging, Chuck turned and saw the two girls wrapped in one-another, an eyebrow arching at the picture. In the blink of an eye the gaze was over though, and soon the boys turned and made their way into the shadows of the enclosed courtyard, a sigh escaping Blair's lips as they did so.

"Tonight I'll be fishing for Bass."

 **~x-X-x~**

"Absolutely not!"

Thick hands dove south and dipped into the pockets of faded denim jeans. Tinkling, metal sang out as fingertips grasped tightly. Pulling the keys out, the older man pushed the key into the heavily bolted door and twisted.

"But Dad, come on. This is my _first_ invitation! Do you know what that _means?_ "

Turning to face his desperate daughter, Rufus Humphrey rolled his eyes in disinterest. For months now his daughter had been running around doing errands for this Waldorf girl without so much as a thank you. He'd never come home to see this famous Blair visiting his darling daughter, in spite of all the extra hours of work she put in trying to please her. He found it extra disturbing that after months of helping out her _so-called_ friend, Jenny was only now receiving an invitation to a party. He'd known sending his children to an Upper East Side school was a gamble, particularly when they resided in the less-affluent area of Brooklyn, but none-the-less he made the decision to put their academic careers and opportunities in front of any misgivings he may have felt regarding the social scene of the Manhattan postcode. However, what he feared the most had actualized before his very eyes, and he now regularly came home to find his daughter slumped over piles of extra work just to get a foot in with some exclusive clique at school. He hated that their address caused his daughter such pain, but what he hated even more was that the mentality of some of the students at school was to look upon his daughter like she was a lesser human being simply because her area code had a few different numbers.

 _And now she as begging to be around them all night?_

"I said no, Jenny." A gruff voice matched the five o'clock shadow that threatened to take over his jawline. "Why would you even want to socialize with these people anyway?" Stepping into the dimly lit Brooklyn loft he shared with his children, Rufus planted his guitar case on the ground and watched as his daughter's face fell into its usual crumpled expression whenever she got an answer she didn't like.

"Dad, you _cannot_ do this to me! It will be social suicide if I don't go after being invited!"

"Oh, I'm sure it's not that bad," the enigmatic father replied, placing his hands on his hips as he stared down at his daughter. Her eyes began to fill to the brim, the water works soon to follow. "Besides, it's a school night."

"We don't have class tomorrow," Jenny replied quickly, doing everything she could to sway her father. "Study day. Come on, _please_ Dad!"

"How do I even know this Blair Waldorf's place is safe?"

"Oh, it's perfectly safe Mr. Humphrey, of that I can assure you."

Whirling around at the husky voice behind him, Rufus nodded his head as he was met with Nate Archibald. Holding a pile of books in his left hand, the boy cut a figure that was both gentlemanly and gorgeous. Biting her lower lip, Jenny couldn't help but smile as he made his way into the living area.

"Hello Nathaniel," Rufus replied, stepping forward as the young boy verged in on the arguing father and daughter. "Studying again?"

"Another tutoring session with _yours truly_ ," came the stoic reply, Dan Humphrey emerging from his room and handing Nate a piece of paper. "We have a quiz on Hemingway next week so I think you should probably revise those notes."

Standing tall with raven hair cut short, Dan Humphrey was the older sibling of Jenny and the quieter of the two. Where Jenny was chasing dreams of becoming social royalty, Dan was more at home reading a book and notching up extra-curricular activities to make his college application look good. When he wasn't doing that, he was helping other students study and working part time in his father's studio to try and scrape as much money together as he could just to get himself to college. Yes, when it came to Dan and Jenny they were as different as apples and oranges.

And they liked it that way. _It kept their worlds firmly distant from each other._

"Thanks man," Nate replied, turning to look at Dan as he folded the paper into his books. "So am I correct in assuming you're uncertain about Blair's back-to-school party?"

"That would be an understatement," Rufus replied solemnly, Jenny's unhappy pout protruding even further outwards. "My daughter wants to go but I'm not so sure-"

"I can assure you, Mr. Humphrey," Nate replied, always the negotiator when it came to uncertain parents. With the baby-faced, sweetness that oozed from his every pore, it was hard not to love him. "Blair has got the safest penthouse in Manhattan and without a doubt your daughter will be perfectly fine." Glaring down at his watch, he quickly shuffled the books within his hold and made his way toward the door. "So will I be seeing you both tonight at Blair's party?"

"Dad?" Jenny asked yet again, the desperation in her tone not having subsided. "Can I go?"

"You can," Rufus replied, meeting his daughter's elated smile as she clapped her hands together in triumph. "Provided your brother does."

Immediately her face fell and she lurched forward, Jenny attaching herself to Dan's arm in an appeal. "Please Dan? _PLEASE?_ "

Looking down at his sister's face, the brooding literary hopeful couldn't help but be swayed by her desperation. Sighing, he looked at his smiling father and relented.

"Alright, alright, I'll take you. But you owe me!"

Cheering, the bubbly blonde wrapped her arms around her brother and planted a huge kiss on his cheek. As she dashed back to her room amidst squeals of delight, Nate laughed as Dan waved goodbye and closed the big studio door behind him. Turning to face a chuckling Rufus, Dan sent a glare his father's way before shaking his head at the thought of spending the night with people he had nothing in common with. A whole night making small talk with people he'd never spoken to in his life.

 _What the hell was he going to do?_

 **~x-X-x~**

 _Thoughts? Scroll down lovely readers and hit REVIEW!_

 _It will make my day!_


	3. RSVP Waldorf

**AN:** Wow! Thanks for all the reviews and follows and kind words. As I said, I am not sure which way I will go. I am a DAIR shipper, but I liked Chair pre-hotel-sale thingy and since this is going back to the start I could go either way. If I had to pick right now, I'd probably say Dair because I like them more but I tend to change my mind as I write so I really couldn't say 100% right now. I'm sorry! If you would rather not wait around then I understand and thank you for your reviews thus far.

Please don't fight with each other though. Everyone is entitled to their opinion and their favourite ship and I respect everyone here! I almost forgot how passionate GG fans and shippers are. _Almost_ lol.

I sincerely hope you like the latest update.

 **Kissing Frogs and Catching Princes**

 _Dedicated to ever-faithful and loyal GG shippers and fans out there._

 **x~X~x**

 **Chapter 3: RSVP Waldorff**

"Blair, I believe this is what they call _above and beyond_."

The latest wine-coloured Louboutin's glided across the darkly stained hardwood floor in quick succession, Serena arriving beside her best friend in a matter of seconds. Reaching down to give Blair a kiss on the cheek, the two girls embraced before the brunette began to smile adoringly, happy with the way her darling and sophisticated Penthouse had been transformed in just a few hours. Cheerful bodies floated all around them as the obvious chatter of happy guests filtered throughout the noise spaces that opened up between the melodious tunes played by the DJ and the barking orders of an enthused and highly-organised hostess. Although it was well known that Blair Waldorff was the best when it came to social gatherings- _people fought with determination and perseverance for months just to get on the waiting list_ \- this one had outdone them all. Ice sculptures glistened in the corners, illuminated by the disco lights that sporadically flickered across the crowd. Sharp streaks of pinks, blues, greens, yellows and purples projected throughout every room and danced over the party-goers, no expense spared. Waiters carried out an endless array of hors douvers, specifically designed to match the tantalizing taste buds of the man in Blair's sights. Anything she could find out about his preferences was on prominent display in her home. Artists and artwork he enjoyed, music he listened to, the brand of scotch he liked- she had gone all out. But she knew it was worth it. A man like Chuck Bass didn't come around very often, and Blair was determined to call him hers.

And she very rarely didn't achieve what she set out to do. In fact, she couldn't recall a moment where she had actually failed.

"It is one of my better accomplishments," the brunette agreed, turning to smile at her stunning friend with complete elation. "And when he walks through those elevator doors he's going to see that not only do I have amazing taste, but I am also the perfect match for him in every way."

Serena chuckled, reaching out and grabbing a glass of champagne as the waiter walked by. He smiled as she took it from him, the skin-tight black dress accentuating her enviable frame. "Blair, how could any man refuse?"

"As usual, you make a good point S."

Reaching for another champagne, Serena plunged the crystal refreshment into Blair's hands and laughed. The two girls clinked their glasses, eyes landing on them as they held onto one-another and glanced around the room. Penelope wandered throughout the crowd and stopped before them, chocolate eyes alight as she pulled out her phone to display an illuminated message from Kati Farkas, the message received with anxious eyes.

" _ **Bass out of water.**_

 _ **Get your reel ready.**_

 _ **5 minutes and counting.**_

 _ **Has won an Archibald prize."**_

"He's with Nate," Blair announced excitedly, Penelope smiling triumphantly as she slid the iPhone back into her lime-green Birkin. Fixing her chocolate locks behind the silken headband that adorned her head, the young girl waited patiently for her next round of orders.

"Penelope, go and make sure that the Macallan 1939 is ready. With ice!"

Penelope nodded and disappeared back through the crowd, Serena grinning at Blair as she witnessed her friend's cheek flush a slight rouge. She reached out and touched her hand, the blonde beauty giving it a slight squeeze for support. Her luscious locks fell over her creamy, bare shoulders and her husky voice was of comfort, as usual.

"See B, he came. Now all you have to do is be your ever-charming self and there is no way he could resist." Her smiled beamed down onto the smartly-dressed social queen beside her and it served to further demonstrate just how genetically blessed Miss Van Der Woodsen really was.

Blair swallowed hard, her eyes darting between her friend and the elevator door as she felt her heart beat ever-so-strongly in her chest. Her mind ticked over with all the ways she was going to respond when she saw him enter. Her poised stance; her devilish smile and her tilted head that revealed a sweet yet seductive side were all definitely a must. If only she could figure out what to start with first when he came in-

 _Ding!_

Sliding out from the mirrored elevator doors, Nate Archibald slid into the party like he was born into it. Soft brown tendrils hung loosely across his forehead, just grazing the tips of his elongated lashes that would make even the most beautiful of supermodels envious. Cerulean orbs danced across the party and fell back into the lift as a thick hand reached out and held onto the doors to cease their advance. Within seconds he was there, sauntering into the party like a Roman God and causing Blair to stop in her tracks and catch her breath.

 _Haaaah. Charles Bass._

His pixie-like darkened hair was prominent, combed loosely across his forehead and resting at the sides of his face. His trademark scarf was absent this time, his body flanked instead with a lemon, long-sleeved business shirt and bone suit pants. A snug V-neck vest sat across his chest, resting nicely at the base of his stomach and splashing his frame with a checkered colouring of red, blue and white. Even his shoes were shinier than anything Blair had ever seen on a man, charcoal like the night and sliding into her apartment with the greatest of ease. It was in that moment that she knew – _Chuck Bass was the one for her_. The dress sense alone was enough to rival even her. She smiled at the thought as Serena threw her delicate hand into the air, catching Nate's attention in a quick wave. Blair cleared her throat and composed herself, Serena squealing ever so slightly beside her as the boys approached.

"Blair, Serena- I'd like you to meet an old friend of mine, Chuck Bass."

Nate smiled as he presented his childhood friend with an open hand pointed towards him, Chuck gazing between both ladies in acknowledgment. He pursed his lips together with a slightly amused smile, a twinkle in his eye as he measured up the two beauties before him.

"Pleasure," Blair announced, her voice slightly high as she sent forth her most encouraging smile. "So glad you could make it to our _little soiree_."

Serena raised an eyebrow at Nate upon hearing Blair speak and he sent her a wink, the smile on his face growing even larger as his gaze lingered on the blonde for a moment. Serena didn't notice, instead turning her attention back to Blair and Chuck in an attempt to be interested in what was being said. No doubt, she would have to go over the conversation with extreme detail the minute they crawled under Blair's overpriced satin sheets that night.

"The pleasure is all mine," Chuck replied, velvety tones hitting the air like a melodic fantasy of Blair's own making. He noticed her eyes firmly planted on him and he loved the attention, Chuck tilting his head to the side as he gazed at her. "I can see you've gone to a lot of trouble and naturally I appreciate the invitation."

He smiled then, his lips pursing together and curling up at the edges ever so slightly. Blair mentally reminded herself to breathe as she gazed at his thick, plump lips, imaging how good it would feel to kiss him. She wondered how she had been so lucky as to have the one person she was obligated to watch over be so strikingly handsome and full of class. She knew she had to be on her game for there would be many-a-pair-of-eyes set upon reeling this Bass in. She flicked her wrist to signal that the party was no trouble at all, as if it were nothing more than a gathering she could organize at any point in time on any given day.

"Not at all," the fiery brunette announced, her cheeks growing a tinge of rouge as she gazed up at him. "It's customary that I throw a welcome back to school gathering at the beginning of the school year. I'm only sorry that it coincided with our get-together."

"You're who my mother organized as a chaperone?" Chuck asked, his eyes relaying his obvious surprise. "Are you sure?"

"Of course," Blair smiled, her eyes lighting up with her usual charm and beauty. She played innocent so very well. "I am always delighted to help out wherever I can."

Chuck's eyes glazed over slightly and he turned to signal to the waiter to bring him a drink. Serena noticed his sudden disinterest and swallowed hard, rattling her brain to think of what else she could do to help her friend.

"Blair is known for her amazing parties," the blonde jumped in, encouraging Nate to join her with a quick flash of her stunning eyes in his direction. She sent Chuck her biggest smile, her beauty a hard force to avoid. "It's one of the many talents she possesses."

"And one of the most useful," Nate agreed, Serena sending him a looking of humorous surprise because he couldn't think of anything better to say. She nudged him slightly, Chuck noticing the exchange between the two and trying his best to hide a satisfied smirk.

"Well come on, who doesn't like to party?" Nate replied, trying his best to still the slight look of dissatisfaction that was currently being sent his way from Blair. "Chuck here loves a good party."

"Indeed," the young boy agreed, turning to Nate and nodding his head. "But a dry party is never a good party-"

"-I think I can help you there," Blair smiled, turning on her heel and moving away from him. She stopped in her tracks and turned, sending Chuck a coy smile as she gazed back at him. "If you're game?"

The move surprised Chuck, his eyebrows rising slightly as he looked her over. She was beautiful for sure and her clothing sense and style was impeccable. She was well-bred and she was seemingly at the top of the social ranking at school. Yet the fact that his own mother had sought Blair out to be his chaperone- a word he used lightly because it always made him feel like a child- was cause for concern. Not to mention that he was back in New York City now and he came with baggage.

 _That baggage could wait one night._

"Sweetheart, I'm _always_ game." He smirked at her then, closing his eyes slightly so that her knees began to wobble slightly under his gaze. "I'm Chuck Bass."

Blair fluttered her eyes at the remark and turned on her heel, all eyes turning to watch as the pair made their way through the moving bodies of the school's student body. Chuck noticed each time Blair sporadically turned around to check if he was still there and it made him laugh a little inside. She was a good little girl, wasn't she? He had to admit, when his father had told him he was to be escorted out the first night at his new school, he was against it. He was more than capable of finding his way throughout the city and doing as he pleased. However, Bart Bass was a tyrant who seemingly didn't care for what his son wanted and so that was that. He could hear his father's voice now, disapproving in its tone as he spoke to him earlier today.

" _Don't embarrass me today, son. I don't want to hear that you've pulled any of the same crap that you did last time or I will send you straight back to boarding school. Got it?"_

Chuck had merely looked at him and returned to his morning paper, the eggs benedict going cold before him. He didn't care for his father's rules and he didn't care for being set up. Yet when he arrived at Blair's house, he had to admit he was pleasantly surprised. Clearly, she was wealthy. Or at least her parents were. Classics hung from the ceilings, rimmed in gold and depicting various eras. Hell, even the clothing the brunette wore could have been an art form in itself and he was rather fond of fashion. Now he could add excellent taste in liquor as she summoned a girl towards her, the raven-haired beauty smiling cheekily as she looked upon Chuck and handed Blair the tumbler. She turned and held it out to him, a faux-innocent look on her face as she spoke.

"I assume you drink the 1939?"

"Whenever I get the chance," Chuck smiled, bringing the ten thousand dollar whisky to his lips. It sailed down his throat, the smoothest of textures and taking him back to his happy place. He toyed with his glass, his finger dancing around the rim, flowing in circles as he looked at Blair. She was beautiful, there was no denying that – but was she the type to go to the same limit? There was only one way to find out.

"Blair, can I interest you in some fresh air?"

He held his hand to his mouth, pulling his fingers together and mimicking the action of smoking whilst reaching out and gently stroking the flesh of her arm. His touch tingled and Blair stopped in her tracks, round eyes falling slightly as she contemplated his request. He could tell in that instant that she wasn't the type to spark up and he breathed out slowly, nodding his head in understanding as her eyes began to light up with awkwardness.

"Of course," Chuck replied, holding his hands up as he stepped back. "It's not your style. I understand."

"No, I just-" Bair replied, scrambling to find something to say. "I just, um-"

The elevator sounded off in the background, Blair's eyes turning frantically towards the sound. An enthralled and obviously nervous Jenny Humphrey emerged, her large eyes gazing in awe at the penthouse she had just stepped into. She clutched a tiny white purse at her side, her ashy, blonde hair dangling loosely over the pink cardigan she had draped on. Even in flat shoes, she was remarkably tall and incredibly thin. Yet it was obvious that she was different to the people around her. Her clothes were unrecognizable, her floral dress wrapped in a plastic belt at the top off her waist. She was a pretty girl – but she was also clearly not in the same league as those around her.

All except the bumbling boy that stepped out of the elevator behind her, much to Blair's surprise.

"- I have to go deal with _that_ ," Blair replied, pointing towards Jenny and Dan as they awkwardly wandered through the crowd of people who stared in confusion at them. She turned before Chuck could reply, striding past Serena and Nate who had found a quiet corner to talk in and right into Jenny's path, her eyes alive with questions that the young blonde knew to expect.

"Why, hello Jenny," Blair spoke sweetly, although her faux-smile demonstrated she was feeling anything but. "What are you doing?"

Jenny stumbled on her words, the notoriety of the girl before her well known and established since kindergarten.

"I'm sorry, I thought you said it was okay that I come-"

"-I remember," Blair cut her off, pursing her lips as she stared at Kenny. "But I don't remember it being a plus-one?"

Dan turned and looked at Blair then, a look of total disinterest and lack of enthusiasm sprayed all across his boyish features. Serena stopped her conversation with Nate and looked up at the trip, curious to see what Blair was doing. She gazed at Dan, an interest piqued as she watched his total lack of fear when speaking to her best friend, a look that was rarely seen on anyone.

"Well our father isn't like the parents of you and all your little friends so he actually cares that his teenage daughter gets home safely."

Jenny nudged her older brother in the ribs in horror, the chocolate-haired scholar flinching slightly at her touch.

"Dan-"

"Oh, you had to be chaperoned by your brother?" Blair smirked, a light scoff escaping her lips as she looked down on them both. It was clear she had a distaste for what was before her and she was making no effort to hide it. Dan recognized the look. He had seen it many times at St Jude's. "That is the lamest thing I've ever heard, Jenny."

Jenny held her tongue and lowered her head slightly, Serena jumping up from her seated position with Nate and floating across the floor to her best friend. She fell in Blair her and gripped onto her forearm, smiling infectiously at Dan who couldn't help but smile back.

"Come on, B." Serena smiled sweetly, pulling her friend on the arm slightly to encourage her. She knew exactly how to defuse this situation and she was going to use every trick she knew. "Jenny worked really hard getting you the information you needed tonight so I think you just focus on the task at hand and leave Jenny to enjoy herself."

"And what about this one," Blair complained, raising her eyebrows as she looked at Dan in distaste. "What am I supposed to do with him?"

" _Do_ with me?" Dan questioned her, looking at Blair with a mixture of confusion and contempt. "I'm not a dog. I won't pee on your sofa or anything-"

"-We can hang out," Serena interrupted, Dan stopping mid-sentence at her rather amazing offer. "I'll be more than happy to get to know um-" She waved her hands and looked at the eldest Humphrey in expectation, Dan clearly his throat and giving her the information she needed.

"Uh, Dan. I'm Dan Humphrey."

"Dan Humphrey," Serena grinned, her perfect teeth glistening as she extended her hand out to him and said his name. "See , we're already friends."

Dan smiled and shook her hand, unaware of the wary pair of eyes that watched them from behind. Serena turned and shooed Blair away, nodding for Jenny to make a quick exit behind them as she turned her attention onto Blair.

"Now go," the beautiful blonde encouraged, pushing her friend backwards slightly to encourage her own retreat. "You've got a Bass to catch." Blair mouthed the word 'thank you' and walked away, her perfectly-designed body weaving its way through the crowd and out of sight. Dan cleared his throat and nodded in Serena's direction, pursing his lips together as awkward held his hands in front of him.

"Thanks for the save," he began, smiling slightly despite the fact that his voice was slightly dismissive. "You can go an enjoy the party now."

Serena smiled in confusion, her wavy, golden locks falling loosely yet in a perfect movement across her creamy shoulders.

"I just mean," Dan stammered, trying to get the words out correctly. It was strange, he'd never had a problem expressing himself before but something about this girl made him incredibly nervous. "You don't have to babysit me tonight. I know we're not friends and I know you were just trying to help my sister out- which I am actually really grateful for because she can succumb to pressure sometimes and I get the feeling that Blair can be quite dominant and I just want to make sure my sister-"

He stopped when he saw Serena smirking at him, clearly trying her best not to laugh.

"-And I'm clearly talking too much," Dan replied, taking a step back and nodding his head in acknowledgement. "Anyway, I'm just saying-"

"Would you like to have a drink with me?" Serena asked suddenly, cutting him short before he could stumble over any more run-on sentences. Dan looked at her in surprise, unsure what to say. He had never spoken to anyone from this social ranking before and he had never felt the need to. The trouble with that logic though, was that it didn't prepare him for a moment like this and because he was unprepared, he remained silent.

 _And he felt like a prize idiot._

"It's just a drink," Serena smiled, holding her hand out and giggling like a little school girl when he had trouble taking it. She rolled her eyes and grabbed his hand, pulling the shocked boy towards her so that her lips were at his ear.

"Come on," she whispered, the sweet smell of vanilla filling Dan's senses as her aroma invaded him. "I know where Mrs. Waldorff keeps the good stuff."

And without so much as waiting for a reply, Serena Van Der Woodsen was pulling Dan Humphrey, a social nobody, up the tall flight of stairs that lead to the bedrooms and away from the confused gasps of the crowd, Nate standing to his feet and watching them leave with a look of utter annoyance on his face.

 **x~X~x**

 _Please review and let me know what you think xo_


	4. Into The Lion's Den

**AN:** This chapter was so hard to write because everyone gave so many opinions about what kind of story this should be that I got lost writing it. So I just had to take a break and come back to it when I knew where I wanted it to go for now. I hope you all enjoy it.

Thanks to everyone who reviewed, favourited and followed. It means a lot xo

 **Kissing Frogs and Catching Princes**

 _Dedicated to ever-faithful and loyal GG shippers and fans out there._

 **x~X~x**

 **Chapter 4: Into The Lion's Den**

"I won't bite."

Yet that is exactly what she did, warm alluring eyes gazing up at Dan Humphrey with an air of cheekiness as Serena van Der Wooden flopped onto the bed of the upstairs room that they had somehow found themselves inside and bit down on her lower lip.

"I know that. I'm just-" he stumbled on his words, the ever-poetic and highly-intelligent writer never experiencing such a thing before. It infuriated him, the way his body fluttered and his brain muddled. _What the hell was happening?_

"Just?" she challenged him, a smirk sliding across her angelic features as she tilted her head back and allowed her blonde tresses to dance across the satin covers below her, one leg curving up and over the other knee so that they were crossed and on full display. Not that he wouldn't have notice her ever-popular pins had she not had them right in front of him. They were practically their own personality with how famous they were.

"I'm just trying to figure out what the hell I'm doing up here?" Dan answered back, ever pragmatic and straight to the point. His eyes looked confused and his head darted from one wall to the next, taking in the scenery. The room looked like it had come straight out of a magazine. He certainly didn't know which magazine, but he was certain his sister could figure it out within a matter of seconds.

 _He and Jenny were so absurdly different in every way and yet she was the most important person in his world._

And this world, the weird place he had suddenly entered into with the most popular girl in school, was definitely not his. But for some strange reason that he could not fathom, she longed for it to be hers and since he had never been able to say no to his darling sibling, here he was stumbling through the abyss of popularity and poison.

"I asked if you wanted a drink." Serena announced, patting the bed beside her and ushering him to sit. "What is so complicated about that?"

"Um, how about the complete lack of beverages in this room?" Dan replied, sliding to the spot next to her and trying his best to center himself. He cleared his throat and she giggled, melodic like a little girl who had somehow managed to get all the boys in the street to do her bidding. He had no doubt Serena could do the same.

"Okay," she sighed, raising her hands before her in defeat. "You're right. I didn't ask you up here for a drink."

"Then why am I here?"

He was direct and to the point and unlike any boy she had met. Well, some parts of him were the same as the others, like the way he stared at her and the way she responded to the attention. Those things were identical to everything she had ever experienced with a boy. But the nervousness he carried with him – _the uncertainty of being around her_ – _**that**_ was completely brand new.

"You intrigue me," came the surprising reply, Serena slinking onto one arm and leaning in slightly closer to Dan. She smelt liked flowers in Spring. "And I don't get that from people very often."

"I doubt that very much," Dan replied, swallowing hard as he looked at the beautiful girl before him. There was no way with the hype that surrounded this girl that she would have ever fail to be intrigued by the people that entered her life. Here would have been too many to even make that possible.

"Why?" she asked, turning to face him directly. Her eyes bore into his and he could see her genuine curiosity for his reply, something he'd never expected. What the hell was this night turning into?

"You just seem like the kind of girl who we seen lot of things," Dan replied, coughing slightly to clear his throat as the familiar wave of nervousness entered his body again. Damn, she was so close he could reach out and touch her. "I doubt anything could surprise you these days."

Serena smiled slightly, a touch of sadness entering her eyes as she pulled them away from him. He panicked slightly then, worried he had perhaps said the wrong thing, that deep down he may have heard stories about the way the school's elite carried out their envious lives but that somehow he had been misinformed when it came to her, a girl he had seen but never spent more than five seconds speaking to.

"I'm sorry if what I said has upset you. I honestly didn't mean-"

"You didn't," Serena replied, running her right hand through her enviously-long tresses and leaning backwards on the bed, both palms resting on the soft blankets below. "I'm used to people thinking I'm that kind of girl-"

Oh _god_ , no!" Dan sputtered, the sound of horror in voice enough to make Serena do an about-face and look at him with surprise. "I would never dream of implying that you were some kind of, some kind of, um-"

"Whore?" Serena smiled, his obvious fear at her reply softening the small amount of anger she had previously felt. If only he knew that was what most people thought about her anyway. _Serena Van Der Woodsen – beautiful, rich and a total whore!_

"I've never seen you that way," Dan immediately replied, swallowing hard as he looked at the blonde goddess before him. Serena stopped for a moment, her eyes glazing over in confusion as Dan spoke to her. Her confusion then in turn confused, the young brooding boy perplexed at how anyone could see Serena as anything other than amazing.

They were so wrong about her. _All of them._ He knew there was more to her than she let anyone see. He reached out and took her hand, unaware of the pair of eyes that watched them from the door behind.

"I'm genuinely sorry."

"You are the only person I've met that has ever apologized to me for anything," Serena smiled, turning back to him and throwing the full force of her allure in his direction. She looked down at their hands entwined, his soft thumb rubbing against her skin in the most beautiful way. How had this happened so suddenly? She only had to get him up to the room to give Jenny a shot at enjoying the party without Blair's antics and yet here she was, enjoying the company of Jenny's big brother. Dan, a boy who had never even been on her radar. A boy she'd never noticed before and yet he was fast becoming a boy who intrigued her.

And that rarely happened to her. _Not with her mundane life._

"Where did you come from, Dan Humphrey?"

"Brooklyn," he replied, his face twitching in pain as he openly chastised himself for his ridiculous reply. She laughed again, enjoying his uncomfortableness around her. The way he looked at her was unlike any way a boy had looked at her before. _She liked it,_ _ **a lot**_ _._ This party had fast become one of her favorites of the year.

"Dan Humphrey from Brooklyn," Serena cooed, her words sweet like honey as she leaned closer to Dan so that their eyes were directly staring into one another's. "It's nice to meet you."

 **x~X~x**

The party was a raging success. Bodies weaved in and out of one-another in drunken stupor and the music was perfectly fitting for the evening's festivities. Glasses clinked as the alcohol continued to make its rounds around the enviable penthouse and laughter, chatter and idle gossip flowed throughout the abode like wildfire. It was typical Waldorf gathering and it was everything the young fashionista had promised. Yet Blair couldn't enjoy it, chocolate orbs flowing throughout the bodies of her peers with a slight aura of panic as Penelope returned with wide eyes and fear.

"Well?" Blair snapped, brows furrowing as she looked at her minion with distaste. "Where is he?"

"I couldn't find him," Penelope grimaced, clearly uncomfortable as she stood before the school's queen. Rightfully so, Blair was a force to be reckoned with, even on her worst day. The brunette smiled painfully, perfectly white teeth on full display as she leaned forward and wrapped her arm around the girl before her, leaning in close and dragging her by the elbow down the hallway. They weaved in and out of the school's elite, the Waldorf heir ensuring that curious eyes were only met with a smile and plastered calmness. Pulling Penelope into the kitchen, Blair waved off the server that lingered and waited for the door to swing shut behind them, intent eyes staring at a quivering and reluctant girl before her.

"What do you mean, you couldn't _find_ him? The place isn't that big. Do I need to draw you a map?"

"No Blair," Penelope squirmed, biting her lip in panic as the fiery brunette glared down at her. "But I looked everywhere. I looked in every room, on the terrace, in the lobby – I think that maybe, he's gone home?"

Blair swallowed hard and closed her eyes, willing not to lose her cool as the anger and resentment raged within her. Why did this have to be so damn hard? Why did she have to be the one who had to work tirelessly to get what she wanted in life? Everything simply fell into Serena's lap and yet Blair had to fight for it. It was lucky she loved her best friend so much because any normal person would be consumed with jealousy and rage.

"Obviously, I have to do everything myself. Cleary, you're not ready for the responsibility I handed to you."

She clenched her fists together silently, Penelope looking down and taking a slight step back. Intimidation was Blair's most fascinatingly terrifying trait. It's what got her what she wanted and where she needed to be. She strong, smart and cunning and she wasn't going to apologize for it. She just needed people who were smart enough to follow her lead.

When Blair opened her eyes she looked straight at her pathetic excuse for a minion and shooed her away, the young girl's heels clicking across the floor as she darted out of the kitchen with haste. Blair closed her eyes once more and straightened the headband that rested at the top of her head, a long breath exhaling from her lips as she steadied herself.

"Interesting."

Blair jumped at the sudden voice behind her, the velvety-soft tones floating across the air and landing on her ears in a mixture of ecstasy and longing. She turned on the spot and blinked, Chuck leaning against the metallic bench top with a look of intrigue splattered across his features. In his hand he held a sandwich, his fingers perfectly wrapped around the bread and exposing the silver ring that adorned his finger.

Blair looked at him indignantly, turning her body so that her svelte legs were on full display as motioned with her eyes at the sandwich in his hand.

"A sandwich? That is your choice of snack with everything else that is available tonight?" Chuck pushed himself off the bench and stepped towards her, Blair's eyes indignant as she tried her best to put on her strongest front. She heard he liked a challenge and she could be his biggest one yet.

"I had the munchies," he cooed, sliding up before her and looking down into her eyes. "I always had a thing for truffle oil." He leaned in closer still, his breath warm on Blair's neck. She felt a thrill race through her, the hairs all over her body sticking up on end. "It's strong, delicious."

Chuck smiled as she stood there, immobilized with uncertainty. He loved this part about women, the way they trembled in his wake. It gave him a rush, a euphoric dash of adrenalin like a lion closing in on its prey. Blair Waldorf would be his greatest victory yet.

"Dressing up sandwich with truffle oil doesn't change the fact that it's bread." She turned and looked at him then, a fire in her eyes that he hadn't seen before. _She was defying him?_ This was different for the famous Bass and somehow he found himself drawn into a sparring match with the least likely of opponents.

"Interesting."

"Yes," Blair replied, a small smile of accomplishment rippling across her face as she looked at him. He could smell the Chanel that traipsed her skin, the scent invading his senses and working its magic on his groin. _Exactly as she had no doubt intended_. "I am."

He knew what she thought of him, Nathaniel couldn't have been more obvious of the fact as he mumbled his way through Chuck's need to be at this particular party this evening. He had humored his friend simply because they had known each other since they were kids and their fathers were long friends. He hadn't expected much else from the night's festivities. Blair was known to be a power-hungry socialite and he had seen so many of those in his lifetime. Hell, he had bedded more than half of them. But something about her was different. That evening she had pulled out all the stops to impress him and yet when they were alone she was anything but flattering and attentive. She was defiant, strong and fierce.

And he enjoyed the hell out of it.

""So tell me," Chuck reached out and brushed Blair's hair behind her cheek, his hand falling down to rest on her creamy, exposed shoulder. "When are we going to get to the part where you invite me to your room?"

Blair swallowed hard and looked down at his hand on her left shoulder. She could feel his thumb tracing circles on her skin, warm to the touch.

"How about half-past never?" Blair announced, sliding his hand off of her shoulder and staring at him coldly. She raised her eyebrows, seemingly bored from his offer. This wasn't how they were going to be. This wasn't what she had pictured. Chuck Bass was going to see her as a viable companion, not a one-night-stand he could add to the little black book he kept in his side drawer.

"Come now, Blair," Chuck replied, smiling down upon her and hitting her with the full weight of his charm. She bit her bottom lip and his smile widened at the move, internally congratulating himself on being so persuasive. "We both know this is what you wanted."

Blair smiled and reached up, her lips closing in on his as he closed his eyes. Her hand slid down to his chest, landing there so that she could feel his heat beating beneath the silken fabric that adorned it. His breath felt warm as she came closer and it took all her strength not to give into him right then and there.

But she was Blair Waldorf. She was the queen of Constance, the heir of Waldport designs and the socialite goddess of the Upper East Side. She was nobody's conquest.

 _Nobody, not even Chuck Bass, was going to change that._

"If that's what you really think," Blair breathed, her lips touching his cheek in the smallest and briefest of kisses. "You're not as smart and charming as I thought you were. _Interesting_."

With that she turned on her wine-infused heels, Louboutins melodically clicking the tiles beneath as she walked away from him. Chuck smiled as he opened his eyes and watched her leave, her small glance back at him revealing a devilish smirk as he nodded his head in approval. She was definitely not who he expected her to be and it excited him. He had thought boarding the plane that coming back and being home would be as boring and mundane as when he had left it, but meeting Blair had just gone to show that appearances could be deceiving.

And Charles Bass loved a good game of deceit.

 _Game on, Blair Waldorf!_

 _Please review and let me know what you think xo_


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